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1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline and preparation method and application thereof

A quinoxaline and hydroxyethyl technology, which is applied in the field of 1-oxo-2-methyl-3-(1-hydroxyethyl) quinoxaline and its preparation, can solve rough detection and cannot accurately reflect acetyl methyl Quine metabolism, inability to accurately reflect the residual content of methaquine, etc.

Inactive Publication Date: 2011-05-25
GENIFARM LAB INC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, relying solely on the detection results of a primary metabolite cannot accurately reflect the residual content of acemethaquine. Therefore, the existing technology can only roughly detect the metabolism and residue of acemethaquine in animals, and cannot accurately reflect the acemetquine residue. The metabolism in animals is not conducive to people's research on the pharmacokinetics of acemethaquine in animals and its residue elimination rules.

Method used

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  • 1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline and preparation method and application thereof
  • 1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline and preparation method and application thereof
  • 1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0039] Add 7.5 grams of acemetquine and 200 milliliters of 60 volume % ethanol aqueous solution to the reactor respectively, add 50 grams of sodium dithionite in batches to react at 80 ° C within half an hour, stir and react at 80 ° C for 3 hours, filter, Purified to obtain 3-methyl-2-(acetyl)-quinoxaline with a yield of 88%;

[0040] Add 1.2 grams of 3-methyl-2-(acetyl)-quinoxaline and 12 milliliters of 95% by volume ethanol aqueous solution to the reactor respectively, add 0.4 grams of sodium cyanoborohydride at 25°C, and react at 25°C After 1 hour, the solvent was removed, washed, extracted, and dried to obtain 2-(1-hydroxyethyl)-3-methyl-quinoxaline with a yield of 95%;

[0041]Add 1.2 grams of 3-methyl-2-(1-hydroxyethyl)-quinoxaline and 1.2 grams of m-chloroperoxybenzoic acid to the reactor and mix them at 0°C, then slowly rise to 25°C after 15 minutes to continue React for 8 hours, add 30 milliliters of 10% by weight sodium carbonate solution after the reaction is finis...

Embodiment 2

[0043] Add 7.5 grams of acemethaquine and 200 milliliters of 80 volume % ethanol aqueous solution to the reactor respectively, add 60 grams of sodium dithionite in batches to react within half an hour at 100 ° C, stir and react at 80 ° C for 5 hours, filter, Purified to obtain 3-methyl-2-(acetyl)-quinoxaline with a yield of 72%;

[0044] Add 1.2 grams of 3-methyl-2-(acetyl)-quinoxaline and 12 milliliters of 95% by volume tetrahydrofuran aqueous solution to the reactor respectively, add 0.54 grams of sodium cyanoborohydride at 25°C, and react at 25°C After 0.5 hour, the solvent was removed, washed, extracted, and dried to obtain 2-(1-hydroxyethyl)-3-methyl-quinoxaline with a yield of 99%.

[0045] 1.2 grams of 3-methyl-2-(1-hydroxyethyl)-quinoxaline and 1.0 grams of peroxybenzoic acid were added to the reactor and mixed at 0°C. After 15 minutes, it was slowly raised to 25°C to continue the reaction for 12 After the reaction was completed, 30 milliliters of 10% by weight sodium...

Embodiment 3

[0050] After 4 hours of intramuscular injection of acemethaquine in healthy pigs, blood samples were collected, extracted 3 times with organic solvents, blown dry with nitrogen, and added mobile phase to make a sample solution; another blood sample from untreated healthy pigs was prepared as a blank control according to the above method ; Take compound (I) and add mobile phase to make 1mg / mL reference substance solution.

[0051] High-performance liquid chromatography: UltiMate3000 American Diane Company; chromatographic conditions: Hypersil BDS C 18 Chromatographic column, 250 mm×4.6 mm×5 μm, column temperature: 30 ℃; mobile phase: methanol (B) / water (containing 0.01% formic acid) (A), gradient elution: 0-40 min, 20%-35 % B; 40-45 min, 35%-60% B; 45-57 min, 60% B; 57-60 min, 60%-20% B; 60-65 min, 20% B; flow rate: 1 mL / min, detection wavelength: 241 nm.

[0052] The retention time of compound I was 19.87min, the peak appeared in the sample solution at 19.93min, and the ...

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Abstract

The invention discloses 1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline, a preparation method and application thereof. The 1-oxo-2-methyl-3-(1-ethoxyl)-quinoxaline has a structure shown as a formula (I). The method for preparing the product (I) comprises the steps of: taking maquindox as a raw material, and obtaining 3-methyl-2-(acetyl)-quinoxaline through a reduction reaction; then obtaining 2-(1-ethoxyl)-3-methyl-quinoxaline through a one-step reduction reaction; and finally, reacting an obtained product with an oxidant to obtain the product (I). The product (I) can be taken as a residual marker of the metabolism of the maquindox in the bodies of target animals or a standard substance or reference substance for detecting maquindox residue in animal derived food.

Description

technical field [0001] The invention belongs to the technical field of veterinary pharmacology, toxicology and chemical synthesis, and specifically relates to 1-oxo-2-methyl-3-(1-hydroxyethyl)quinoxaline and its preparation method and application. Background technique [0002] Acetylmethylquine is commonly known as "Shibajing", and its chemical name is 1,4-dioxo-3-methyl-2-acetyl-quinoxaline. It is a carbadox analog and is the first therapeutic antibacterial drug to be marketed in China. , has a strong inhibitory effect on a variety of bacteria, especially on Gram-negative bacteria, such as Pasteurella, Escherichia coli, Salmonella, and Listeria. The first-choice drug and specific drug for chronic dysentery (swine dysentery). Through large-scale popularization and application and clinical observation, it is proved that the drug has the characteristics of small dosage, quick effect, high curative effect, safety and reliability, low cost and convenient use in the treatment of...

Claims

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Application Information

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IPC IPC(8): C07D241/52G01N30/02
Inventor 王永东曾振灵祝诗发操基元刘迎春丁焕中曾东平方炳虎
Owner GENIFARM LAB INC
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